Steven moved to Montreal in 1975 where he joined the jazz vocal group Bug Alley Band featuring singer Karen Young. He was the group's guitarist and one of four vocalists as well as arranger. Bug Alley went on to appear on a number radio and TV shows, the Lotto Canada Show among them, and made recordings for CBC radio. Their album was produced by bassist Gene Perla on PM Records.
In 1980 he became active in the Bay Area music scene after relocating to Oakland CA. This brought him together with players such as pianist Mark Levine, bassist Robb Fisher, and drummer Vince Lateano. He performed in the 1981 Monterey Jazz Festival and played a stint with legendary Chet Baker in 1983. Steven was the jazz guitar instructor for the Young Musicians Program at UC Berkeley during that time.
After moving back to NYC Steven continued his music studies taking composition at the Manhattan School of Music and City University of New York - Hunter College music program where he earned his Bachelors and Masters degrees.
Steven lives in Toronto and leads his own ensembles Steven Cole group and 25 Strings guitar group. He has performed with many of Toronto's fine jazz artists and bands such as John Cheesman Orchestra, Bruce Cassidy's Hotfoot Orchestra and Mbaqanga, Brownman, Kingsley Ettienne, and Toronto Art Orchestra, among others. Steven currently teaches guitar privately and at Merriam School of Music.